5,17-Dibromo-26,28-dihy­droxy-25,27-diprop­oxy-2,8,14,20-tetra­thia­calix[4]arene

Liu, L.-L.; Chen, L.-S.; Ma, J.-P.; Guo, D.-S.

doi:10.1107/S1600536811013043

Volume 67
Part 5
Pages o1110-o1111
May 2011

Received 12 March 2011
Accepted 7 April 2011
Online 13 April 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.041
wR = 0.108
Data-to-parameter ratio = 15.1
Details

5,17-Dibromo-26,28-dihydroxy-25,27-dipropoxy-2,8,14,20-tetrathiacalix[4]arene

Ling-Ling Liu,^a Lu-Sheng Chen,^a Jian-Ping Ma ^a and Dian-Shun Guo ^a ^*

^aDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
Correspondence e-mail: chdsguo@sdnu.edu.cn

In the title compound, C₃₀H₂₆Br₂O₄S₄, the thiacalix[4]arene unit adopts a pinched cone conformation, with one of the ether-substituted rings bent towards the calix cavity and the two phenolic rings bent outwards. The phenyl rings make dihedral angles of 27.12 (9), 36.71 (10), 75.04 (8), and 76.01 (7)° with the virtual plane defined by the four bridging S atoms. The two opposite ether-substituted rings are almost parallel to each other, with an interplanar anagle of 2.99 (12)°, while the two phenolic rings are nearly perpendicular to each other, making a dihedral angle of 74.52 (11)° and a BrBr distance of 13.17 (2) Å. Two intramolecular O-HO hydrogen bonds between the OH groups and the same ether O atom stabilize the cone conformation. In the crystal, two different chains of molecules, one with alternating and the other with tail-to-tail orientations, are formed by intermolecular offset-face-to-face [pi] - [pi] stacking interactions with distances of 3.606 (3) to 4.488 (4) Å between the centroids of the aromatic rings.

Related literature

For general background to the chemistry of thiacalix[4]arenes, see: Shokova & Kovalev (2003); Lhoták (2004); Morohashi et al. (2006); Kajiwara et al. (2007); Guo et al. (2007). For the synthesis and related structures, see: Lhoták et al. (2001); Kasyan et al. (2003); Desroches et al. (2004); Kasyan et al. (2006); Morohashi et al. (2006); Xu et al. (2008); Chen et al. (2010). For [pi] - [pi] stacking interactions, see: Tsuzuki et al. (2002).

Experimental

Crystal data

C₃₀H₂₆Br₂O₄S₄
M_r = 738.57
Triclinic, $[P \overline 1]$
a = 9.3788 (16) Å
b = 11.712 (2) Å
c = 14.768 (3) Å
= 97.904 (2)°
= 95.614 (1)°
= 107.738 (2)°
V = 1513.5 (4) Å³
Z = 2
Mo K radiation
= 2.99 mm^-1
T = 298 K
0.29 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999) T_min = 0.478, T_max = 0.586
7993 measured reflections
5513 independent reflections
4162 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.108
S = 1.05
5513 reflections
365 parameters
H-atom parameters constrained
_max = 0.74 e Å^-3
_min = -0.54 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H4AO3	0.82	2.20	2.926 (3)	148
O2-H2AO3	0.82	2.12	2.849 (3)	148

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2275 ).

Acknowledgements

Financial support from the National Natural Science Foundation of China (grant No. 20572064) and the Natural Science Foundation of Shandong Province (grant No. ZR2010BM022) is gratefully acknowledged.

References

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organic compounds